US4072696AExpiredUtility

5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity

Assignee: SYNTEX INCPriority: Feb 12, 1973Filed: Jan 18, 1974Granted: Feb 7, 1978

Est. expiryFeb 12, 1993(expired)· nominal 20-yr term from priority

Inventors:Colin C. Beard John A. Edwards John H. Fried

C07C 335/28

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Claims

Abstract

Carbalkoxythioureidobenzene derivatives represented by the following formula: ##STR1## where R is a lower alkyl group having 1 to 4 carbon atoms; R 1 is --SR 2 , --SOR 2 , --SO 2 R 2 , --OR 2 , --SCN, --SC(O)NR 3 R 4 , or --M'(CH 2 ) n MR 7 where n is 1-4; R 2 is lower alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, lower alkenyl or lower alkynyl having 3 to 6 carbon atoms, aralkyl or aryl, provided that when R 1 is --SO 2 R 2 , R 2 is not aralkyl or phenyl; R 3 and R 4 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms; Y is amino, nitro, acylamino where the acyl portion has 1 to 6 carbon atoms, --NHC(O) (CH 2 ) m COOH where m is 1-6, or --NHC(S)NHCOOR; M and M' are independently O, S or ##STR2## and R 7 is lower alkyl having 1 to 4 carbon atoms or aryl. The R 1 substitution is either at the 4- or 5-position. The compounds are useful as pesticides, particularly as anthelmintic and antifungal agents.

Claims

exact text as granted — not AI-modified

What is claimed is: 
     
       1. A compound selected from the group of compounds represented by the formula: ##STR9## where R is a lower alkyl group having 1 to 4 carbon atoms; R 1  is --SR 2 , --SOR 2 , --OR 2 , --SCN, or --M&#39;(CH 2 ) n  MR 7  where n is 1-4; R 2  is lower alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, lower alkenyl or lower alkynyl having 3 to 6 carbon atoms, benzyl or phenyl, provided that when R 1  is --SO 2  R 2 , R 2  is not benzyl or phenyl, provided further that when R 1  is either --SR 2  or --OR 2 , R 2  can not be either alkyl or cycloalkyl; Y is amino, nitro, alkanoylamino having 1 to 6 carbon atoms, --NHC(O) (CH 2 ) m  COOH where m is 1-6, or --NHC(S)NHCOOR; M and M&#39; are independently O, S or ##STR10## and R 7  is lower alkyl having 1 to 4 carbon atoms or phenyl; the R 1  -substitution being at the 4- or 5-position; and the pharmaceutically acceptable salts thereof. 
     
     
       2. The compound of claim 1 wherein the R 1  substituent is at the 4-position. 
     
     
       3. The compound of claim 1 wherein the R 1  substituent is at the 5-position. 
     
     
       4. The compound of claim 1 wherein R 1  is --SR 2 . 
     
     
       5. The compound of claim 1 wherein R 1  is --SOR 2 . 
     
     
       6. The compound of claim 1 wherein R 1  is --SO 2  R 2 . 
     
     
       7. The compound of claim 1 wherein R 1  is --OR 2 . 
     
     
       8. The compound of claim 1 wherein R 1  is --SCN. 
     
     
       9. The compound of claim 1 wherein R 1  is --O(CH 2 ) n  OR 7 . 
     
     
       10. The compound of claim 1 wherein R 1  is --O(CH 2 ) n  SR 7 . 
     
     
       11. The compound of claim 1 wherein R 1  is --S(CH 2 ) n  OR 7 . 
     
     
       12. The compound of claim 1 wherein R 2  is lower alkyl. 
     
     
       13. The compound of claim 1 wherein R 2  is lower alkenyl. 
     
     
       14. The compound of claim 1 wherein R 2  is lower alkynyl. 
     
     
       15. The compound of claim 1 wherein R 1  is --S(CH 2 ) n  SR 7 . 
     
     
       16. The compound of claim 1 wherein R 2  is benzyl. 
     
     
       17. The compound of claim 1 wherein R 2  is phenyl. 
     
     
       18. The compound of claim 1 wherein said compound is 2-amino-1-(3-methoxycarbonyl-2-thioureido)-4-(2-phenoxyethoxy)benzene. 
     
     
       19. The compound of claim 1 wherein 2-amino-1-(3-methoxycarbonyl-2-thioureido)-5-(2-phenoxyethoxy)benzene. 
     
     
       20. The compound of claim 1 wherein Y is amino. 
     
     
       21. The compound of claim 1 wherein Y is nitro. 
     
     
       22. The compound of claim 1 wherein Y is acetamido. 
     
     
       23. The compound of claim 1 wherein Y is --NHC(S)NHCOOR. 
     
     
       24. The compound of claim 1 wherein Y is --NHC(S)NHCOOCH 3 . 
     
     
       25. The compound of claim 1 wherein Y is --NHC(O)(CH 2 ) m  COOH. 
     
     
       26. The compound of claim 1 wherein R is methyl. 
     
     
       27. The compound of claim 1 wherein said compound is 2-amino-1-(3-methoxycarbonyl-2-thioureido)-4-methoxyethylsulfinylbenzene. 
     
     
       28. The compound of claim 1 wherein said compound is 2-amino-1-(3-methoxycarbonyl-2-thioureido)-5-methoxyethylsulfinylbenzene. 
     
     
       29. The compound of claim 1 wherein said compound is 1,2-bis-(3-methoxycarbonyl-2-thioureido)-4-methylsulfinylbenzene. 
     
     
       30. The compound of claim 1 wherein said compound is 1,2-bis-(3-methoxycarbonyl-2-thioureido)-4-thiocyanatobenzene. 
     
     
       31. The compound of claim 1 wherein said compound is 1,2-bis-(3-methoxycarbonyl-2-thioureido)-4-iso-propylsulfinylbenzene. 
     
     
       32. The compound of claim 1 wherein said compound is 1,2-bis-(3-methoxycarbonyl-2-thioureido)-4-n-propylsulfinylbenzene. 
     
     
       33. The compound of claim 1 wherein said compound is 1,2-bis-(3-methoxycarbonyl-2-thioureido)-4-n-butylsulfinylbenzene. 
     
     
       34. The compound of claim 1 wherein said compound is 1,2-bis-(3-methoxycarbonyl-2-thioureido)-4-phenoxybenzene. 
     
     
       35. The compound of claim 1 wherein said compound is 1,2-bis-(3-methoxycarbonyl-2-thioureido)-4-ethylsulfinylbenzene. 
     
     
       36. The compound of claim 1 wherein said compound is 1,2-bis-(3-methoxycarbonyl-2-thioureido-4-methoxymethoxybenzene. 
     
     
       37. The compound of claim 1 wherein said compound is 1,2-bis-(3-methoxycarbonyl-2-thioureido)-4-ethoxymethoxybenzene. 
     
     
       38. The compound of claim 1 wherein said compound is 1,2-bis-(3-methoxycarbonyl-2-thioureido)-4-methoxymethylthiobenzene. 
     
     
       39. The compound of claim 1 wherein said compound is 1-(3-methoxycarbonyl-2-thioureido)-2-amino-4-methoxymethylsulfinylbenzene. 
     
     
       40. The compound of claim 1 wherein said compound is 1,2-bis-(3-methoxycarbonyl-2-thioureido)-4-methylthiomethoxybenzene. 
     
     
       41. The compound of claim 1 wherein said compound is 1-(3-methoxycarbonyl-2-thioureido)-2-amino-5-phenylsulfinylbenzene. 
     
     
       42. The compound of claim 1 wherein said compound is 1-(3-methoxycarbonyl-2-thioureido)-2-amino-4-phenylsulfinylbenzene. 
     
     
       43. The compound of claim 1 wherein said compound is 1-(3-methoxycarbonyl-2-thioureido)-2-amino-5-phenylthiobenzene. 
     
     
       44. The compound of claim 1 wherein said compound is 1-(3-methoxycarbonyl-2-thioureido-2-amino-4-phenylthiobenzene. 
     
     
       45. The compound of claim 1 wherein said compound is 2-acetamido-1-(3-methoxycarbonyl-2-thioureido)-5-benzylthiobenzene. 
     
     
       46. The compound of claim 1 wherein R 1  is ##STR11## 
     
     
       47. The compound of claim 1 wherein R 1  is ##STR12## 
     
     
       48. The compound of claim 1 wherein R 7  is phenyl. 
     
     
       49. The compound of claim 1 wherein R 7  is either methyl or ethyl. 
     
     
       50. The compound of claim 1 wherein said compound is 2-amino-1-(3-methoxycarbonyl-2-thioureido)-5-methoxymethylsulfinylbenzene. 
     
     
       51. 1,2-bis-(3-ethoxycarbonyl-2-thioureido)-4-phenylthiobenzene.

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